Movies Like Playing It Cool

Ranked by shared directors, cast, themes, genre, and era — not just generic recommendations.

Failure to Launch

2006·1h 37m·★ 5.7·Tom Dey

Themes: lying, romcomTMDB recommendsRomance & Comedy

Amélie

2001·2h 2m·★ 8.2·Jean-Pierre Jeunet

Themes: romance, romcomTMDB recommendsComedy & Romance

The Wedding Date

2005·1h 28m·★ 6.1·Clare Kilner

Themes: romance, romcomTMDB recommendsRomance & Comedy

Valentine's Day

2010·2h 5m·★ 5.8·Garry Marshall

Themes: romcom, los angeles, californiaFans also likedStarring Topher Grace

Pretty Woman

1990·2h·★ 7.1·Garry Marshall

TMDB recommendsThemes: romcom, los angeles, californiaRomance & Comedy

Love and Magnets

2004·1h 31m·★ 6.7·Yves Pelletier

Themes: lying, romcom

Breakfast at Tiffany's

1961·1h 55m·★ 7.5·Blake Edwards

TMDB recommendsComedy & Romance

Sabrina

1954·1h 53m·★ 7.6·Billy Wilder

TMDB recommendsComedy & Romance

Hasee Toh Phasee

2014·2h 21m·★ 6.8·Vinil Mathew

TMDB recommendsComedy & Romance

¿Quieres ser mi hijo?

2023·1h 40m·★ 6.0·Ihtzi Hurtado

Fans also likedComedy & Romance

Eternal Sunshine of the Spotless Mind

2004·1h 48m·★ 8.3·Michel Gondry

TMDB recommends

Rebecca

1940·2h 10m·★ 8.0·Alfred Hitchcock

TMDB recommends

The Big Lebowski

1998·1h 57m·★ 8.1·Joel Coen

TMDB recommends

Captain America: The Winter Soldier

2014·2h 16m·★ 7.7·Joe Russo

Both star Chris Evans & Anthony Mackie

All About My Mother

1999·1h 41m·★ 7.8·Pedro Almodóvar

TMDB recommends

The Kissing Booth 2

2020·2h 12m·★ 5.7·Vince Marcello

Fans also likedComedy & Romance

Back to the Future Part III

1990·1h 59m·★ 7.5·Robert Zemeckis

TMDB recommends

Match Point

2005·2h 4m·★ 7.6·Woody Allen

TMDB recommends

My Sassy Girl

2008·1h 32m·★ 6.2·Yann Samuell

Fans also likedComedy & Romance

The Wrong Paris

2025·1h 47m·★ 6.1·Janeen Damian

Fans also likedRomance & Comedy

How Good Is Playing It Cool?

Ratings across IMDb, Rotten Tomatoes, Metacritic, and TMDB, plus our verdict.

Where to Watch Playing It Cool

Streaming, rental, and purchase options across 40+ countries.

CountryUnited States

Type

AllStreamRentBuyTheaters

United States

US

Free with Ads

5

The Roku Channel

Hoopla

Fandango at Home Free

Fawesome

Tubi TV

Rent

2

Amazon Video

Fandango At Home

Buy

3

Amazon DVD / Blu-ray

Amazon Video

Fandango At Home

Available in 28 countries